(S)-3-氨基丁酸甲酯 | 83509-89-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (S)-3-氨基丁酸甲酯
• 英文名称: (S)-methyl 3-aminobutanoate
• 英文别名: methyl (3S)-3-aminobutanoate；methyl (S)-β-aminobutanoate；methyl (S)-3-aminobutanoate；methyl (S)-3-aminobutyrate
• CAS: 83509-89-1
• 化学式: C₅H₁₁NO₂
• mdl: MFCD08058804
• 分子量: 117.148
• InChiKey: SJQZRROQIBFBPS-BYPYZUCNSA-N

物化性质

• 沸点：
  54-55 °C(Press: 13 Torr)
• 密度：
  0.987±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-氨基丁酸甲酯 在 Nishimura catalyst <(45.9% Rh/19.9% Pt) oxide> 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、10.0 MPa 条件下， 以15%的产率得到(S)-3-氨基丁醇
  参考文献：
  名称：

  Catalytic Hydrogenation of Chiral α-Amino and α-Hydroxy Esters at Room Temperature with Nishimura Catalyst without Racemization

  摘要：

  The hydrogenation or carboxylic acid derivatives at room temperature was investigated. With a mixed Rh/Pt oxide (Nishimura catalyst), low to medium activity was observed for various alpha-amino and alpha-hydroxy esters. At 100 bar hydrogen pressure and 10% catalysts loading, high yields or tire desired amino alcohols and diols were obtained without racemization. The most suitable alpha-substituents were NH2, NHR, and 011, whereas beta-NH2 were less effective. Usually, aromatic rings were also hydrogenated, but with the free bases of amino acids as substrates, some selectivity was observed. No reaction was round for alpha-NR2, alpha-OR, and unfunctionalized esters; acids and amides, were also not reduced under these conditions. A working hypothesis for the mode or action of the catalyst is presented.

  DOI：

  10.1002/1615-4169(20011231)343:8<802::aid-adsc802>3.0.co;2-t
• 作为产物：
  描述：

  巴豆酸甲酯 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (S)-3-氨基丁酸甲酯
  参考文献：
  名称：

  α-Alkylation of β-aminobutanoates with lk-1.2-induction

  摘要：

  DOI：

  10.1016/s0040-4039(00)96296-8

文献信息

• A Multifaceted Secondary Structure Mimic Based On Piperidine-piperidinones
  作者：Dongyue Xin、Lisa M. Perez、Thomas R. Ioerger、Kevin Burgess

  DOI：10.1002/anie.201400927

  日期：2014.4.1

  that with ideal secondary structures and real interface regions in PPIs. Scaffold 1 presents amino acid side‐chains that are quite separated from each other, in orientations that closely resemble ideal sheet or helical structures, similar non‐ideal structures at PPI interfaces, and regions of other PPI interfaces where the mimic conformation does not resemble any secondary structure. 68 different PPIs

  极简二级结构模拟物通常被制成类似于蛋白质-蛋白质相互作用 (PPI) 中的一个界面，从而扰乱它。我们最近提出合适的化学型可以直接与界面区域匹配，而无需考虑二级结构。在这里，我们描述了新化学型1的模块化合成，其溶液态构象集合的模拟，以及与理想二级结构和 PPI 中真实界面区域的相关性。脚手架1呈现彼此完全分离的氨基酸侧链，其方向与理想的片状或螺旋结构非常相似，在 PPI 界面具有相似的非理想结构，以及其他 PPI 界面的模拟构象与任何二级结构不相似的区域. 68 种不同的 PPI，其中1 个匹配孔的构象被识别。还提出了一种新方法来确定极简模拟晶体结构与其溶液构象的相关性。因此，dld - 1 faf以比最小能量溶液状态高0.91 kcal mol -1的构象结晶。
• Synthesis of Thioureido-Linked Peptidomimetics, Glycosylated Amino Acids, and Neoglycoconjugates Using Bis(benzotriazolyl)methanethione as Thioacylating Agent
  作者：Vommina Sureshbabu、Gundala Chennakrishnareddy、Hosahalli Hemantha

  DOI：10.1055/s-0029-1219393

  日期：2010.3

  A practical synthesis of thiourea-linked peptidomimetics, glycosylated amino acids, and neoglycoconjugates is described employing bis(benzotriazolyl)methanethione as thiocarbonylating reagent. The entire protocol is mild, efficient, high-yielding, and free from hazardous reagents. All the intermediates and products have been isolated and fully characterized by ¹H NMR, ¹³C NMR, and mass spectrometry.

  本文描述了一种实用的硫脲连接肽模拟物、糖基化氨基酸和新生糖缀合物的综合合成方法，采用双（苯并三唑基）甲烷硫酮作为硫羰基化试剂。整个方案温和、高效、产率高，并且不含危险试剂。所有中间体和产物均已分离并通过¹H NMR、¹³C NMR 和质谱完全表征。
• Enantioface-differentiating (Asymmetric) Hydrogenation of Keto Ester with Modified Nickel Catalyst. XXXII. Structural Requirements of Modifying Reagent and Substrate
  作者：Shinji Okamoto、Tadao Harada、Akira Tai

  DOI：10.1246/bcsj.52.2670

  日期：1979.9

  The enantioface-differentiating hydrogenation of α-, β-, γ-, and δ-keto esters over α-, β-, and γ-amino acid–MRNi has been conducted. The optimum enantio-differentiating power of α-amino acid-MRNi has been found in the hydrogenation of the β-keto ester and that of β-amino acid-MRNi found in the hydrogenation of the γ-keto ester. The results have been explained in terms of the intermolecular recognition between substrate and modifying reagent through the functional groups.

  已进行α-、β-、γ-和δ-酮酯在α-、β-和γ-氨基酸修饰的MRNi上的对映面区分氢化反应。发现α-氨基酸修饰的MRNi在β-酮酯氢化中具有最佳的对映区分能力，而β-氨基酸修饰的MRNi在γ-酮酯氢化中表现出最佳的对映区分能力。这些结果可通过底物与修饰剂通过功能团的分子间识别来解释。
• One-Pot Hydrogenation Conditions for a Sequential Process to (+)-Monomorine
  作者：Guncheol Kim、Sung-do Jung、Eun-ju Lee、Nakjeong Kim

  DOI：10.1021/jo030083c

  日期：2003.6.1

  conditions initiating deprotection followed by intramolecular, sequential reductive amination reactions. The precursors could be prepared concisely using B-alkyl Suzuki cross coupling of a chiral homoallylamine and a vinyl iodide or an iodofuran derivative.

  （+）-Monomorine已在温和的氢化条件下合成，引发脱保护，随后进行分子内顺序还原胺化反应。可以使用手性高烯丙基胺与乙烯基碘或碘呋喃衍生物的B-烷基铃木交叉偶联来简明地制备前体。
• [EN] BICYCLIC PYRIMIDONE COMPOUNDS AS INHIBITORS OF LP-PLA2<br/>[FR] COMPOSÉS DE PYRIMIDONE BICYCLIQUES UTILISÉS EN TANT QU'INHIBITEURS DE LP-PLA2
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2014114249A1

  公开（公告）日：2014-07-31

  The present invention relates to novel pyrimido[1,6-a]pyrimidin-6(2H)-one compounds that inhibit Lp-PLA2 activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases associated with the activity of Lp-PLA2, for example atherosclerosis, Alzheimer's disease.

  本发明涉及一种新型的抑制Lp-PLA2活性的嘧啶并[1,6-a]嘧啶-6(2H)-酮化合物，以及其制备方法、含有它们的组合物和它们在治疗与Lp-PLA2活性相关的疾病，例如动脉粥样硬化、阿尔茨海默病等方面的用途。